The Court Order that Killed "Delete"

Future of Law Newsletter - Issue #2

On May 13, 2025, a federal judge issued a sweeping order: OpenAI must preserve every user chat log, including messages users had deleted, in its copyright fight with The New York Times.

The rationale? Potential evidence.

The message? Deleting data doesn’t make it disappear — or shield it from discovery.

OpenAI complied. Quietly. For weeks, 400 million people kept chatting, thinking “delete” meant gone. When the truth surfaced, so did the backlash.

Trust dropped. And the legal fallout is playing out.

When CEO Sam Altman finally responded, he didn’t back down. He called the court order “inappropriate” and floated a provocative idea: maybe we need “AI privilege” where talking to an AI is protected like a conversation with a doctor or a lawyer.

It’s compelling. Maybe even necessary. But it’s not law. Not yet.

And many in the privacy community are sounding the alarm.

It’s like one of our Goodlawyers, Nofa Khadduri, put it:

“Being told to permanently store every single conversation just in case someone might maybe say something copyright-adjacent? That’s a privacy and compliance nightmare. It’s like demanding your therapist record all your sessions on the off chance someone wants to sue over a story you told.”

“They’re basically arguing that hypothetical infringement trumps real-world privacy obligations — and that flies in the face of data minimization principles and basic decency.”

They’re not wrong. Legal risk is rising and it’s colliding with long-standing privacy norms.

Here’s the current reality:

Enterprise and Zero Data Retention (ZDR) API users are protected. These users have contracts that guarantee their data is wiped and never stored.
Everyone else is exposed. That includes ChatGPT Free, Plus, Pro, Team, and non-ZDR API users. Even “temporary” chats are retained.

The delete button is theater. It changes perception — not liability.

If a court can compel OpenAI to preserve everything, it can compel you. Any organization that stores user data is now in scope.

What should legal leaders do?

Assume deletion is discoverable. If it lives in a log, cache, backup, or vendor system, it can be subpoenaed.
Design privacy into your infrastructure. Don’t let your UI pretend your data practices are clean. Lawyers don’t litigate buttons—they litigate architecture.
Refresh your litigation response muscle. Discovery risk is real. And preservation orders hit systems most teams haven’t even mapped.

The dream of “AI privilege” may become law someday. But today, your best defense is knowing exactly what you keep, and being ready to account for it.

Delete doesn’t mean gone. It means discoverable.

Brett Colvin
CEO, Goodlawyer

Lawyering with Both Sides of Your Brain

By Zak Biggs

After 13 years practicing in BigLaw and in-house, Rebecca Hockin became a lawyer coach and fractional lawyer. We discussed why creativity matters in law and how even six minutes can change everything.

ZB: Why should lawyers care about creativity?

RH: Conventional wisdom is that lawyering is left-brain – logical, analytical, linear. And these skills are valuable. But the profession has doubled down on that mindset to the point where it’s become limiting. We all have a right brain, too. And if we’re not flexing it, we’re leaving a powerful tool on the table.

ZB: How can creativity make lawyers’ lives better?

RH: Lawyers who make space for creative activities – painting, writing, music, or even appreciating architecture – start flexing a different kind of mental muscle. Going to the creativity gym builds tolerance for uncertainty. And that turns into thinking outside the box and generating ideas. It means finding a solution rather than spinning your wheels.

ZB: Can you give an example?

RH: I was in a dance class, and I kept getting thrown off when others were out of rhythm. Then it occurred to me that in some work situations, my timing might have been too fast or too slow. It reminded me how important it is to be aware of the rhythm of the work and the team. I made some changes to my workflow so I can stay in step with my colleagues.

ZB: What’s the simplest habit you’ve seen have a big impact?

RH: Morning Mind Notes! I hear from the lawyers I coach that this improves their mood and performance. Start each day by writing down whatever comes to mind. It doesn’t need to be work-related or even make sense. Just start writing and don’t stop for five minutes. It clears mental space and sharpens focus on what’s most important that day. Think of it as taking a 0.1 for your brain.

ZB: How do you insert creativity into your days?

RH: I start every day with the exercise I just mentioned! I also make time to listen to music, read and write (I’m a word nerd) and go for the occasional adventure with my family.

In addition to working as a lawyer coach, Rebecca Hockin practices as a fractional lawyer through Goodlawyer. You can connect with her on LinkedIn.

LEGAL EVENTS

Goodlawyer Summer Social

Last week we hosted our Summer Social at Woods Restaurant in Toronto. The legal community came out and enjoyed some good conversation and live jazz. Check out our CCO Chad Aboud's photos below!

UPCOMING

ACC Ontario Mid Summer Social
(Toronto, July 24)
Unwind and meet fellow in-house counsel while soaking up the summer vibes at David Rocco. Event is free of charge and for ACC members only.

Goodlawyer at Calgary Cavalry soccer match
(Calgary, September 20)
Join us as we host a group at Spruce Meadows, as the reigning Canadian Premier League Champions host Pacific FC. Reply if interested!

Canadian Legal Summit
(Toronto, October 9)
Hosted by Canadian Lawyer Magazine, this will be one of the biggest legal events of the year. Approved for 5+ hours of CPD. The Goodteam will be there supporting Pauline Chan, who is speaking!

GOOD VIBES

Our Track of the Month is by Supershy. I bet the bassline will make the hair on the back of your neck stand up. Click below for good vibes to fuel your next hour of productivity. –Zak Biggs

Listen on Spotify